Journal
TETRAHEDRON
Volume 61, Issue 16, Pages 4015-4021Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.02.055
Keywords
hydrotalcite; henry reaction; 1,3-dinitropropanes; mechanism; diastereoselectivity
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Commercially available, non-activated 2:1 Mg:Al hydrotalcite catalyzes the nitroaldol reaction between a variety of aromatic and aliphatic aldehydes and simple nitroalkanes such as nitromethane and nitroethane. A new mechanism is proposed for the formation of the 1,3-dinitropropanes. The threo/erythro diastereoselectivity of the nitroethane-adducts was determined by H-1 NMR spectroscopy and was found to range from 50:50 to 70:30. The substituents of the aromatic aldehydes influenced the isomer ratio. (c) 2005 Elsevier Ltd. All rights reserved.
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